1-Hydroxy-2-methoxy-4,5,6a,7-tetrahydro-9,11-dioxa-6-aza-benzo[fg]cyclopenta[b]anthracene-6-carboxylic acid ethyl ester | 206856-40-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 1-Hydroxy-2-methoxy-4,5,6a,7-tetrahydro-9,11-dioxa-6-aza-benzo[fg]cyclopenta[b]anthracene-6-carboxylic acid ethyl ester
• 英文别名: ethyl 19-hydroxy-18-methoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene-13-carboxylate
• CAS: 206856-40-8
• 化学式: C₂₁H₂₁NO₆
• 分子量: 383.401
• InChiKey: BQAUSPVZXWWZQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-Hydroxy-2-methoxy-4,5,6a,7-tetrahydro-9,11-dioxa-6-aza-benzo[fg]cyclopenta[b]anthracene-6-carboxylic acid ethyl ester 在 吡啶 、 lead(IV) acetate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.83h， 生成 Acetic acid (4R,6aR)-1-hydroxy-2-methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-9,11-dioxa-6-aza-benzo[fg]cyclopenta[b]anthracen-4-yl ester
  参考文献：
  名称：

  Ogasawara, Hiromichi; Suzuki, Masaji; Shiohara, Tomohiro, Heterocycles, 1998, vol. 47, # 2, p. 911 - 919

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Benzo[1,3]dioxol-5-ylmethyl-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 在 lead(IV) acetate 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 生成 1-Hydroxy-2-methoxy-4,5,6a,7-tetrahydro-9,11-dioxa-6-aza-benzo[fg]cyclopenta[b]anthracene-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Ogasawara, Hiromichi; Suzuki, Masaji; Shiohara, Tomohiro, Heterocycles, 1998, vol. 47, # 2, p. 911 - 919

  摘要：

  DOI：

文献信息

• (±)-Nantenine analogs as antagonists at human 5-HT2A receptors: C1 and flexible congeners
  作者：Sandeep Chaudhary、Stevan Pecic、Onica LeGendre、Hérnan A. Navarro、Wayne W. Harding

  DOI：10.1016/j.bmcl.2009.03.048

  日期：2009.5

  C1 and flexible analogs of (+/-)-nantenine were synthesized and evaluated for antagonist activity at human 5-HT(2)A receptors in a calcium mobilization assay. This work has resulted in the identification of the most potent 5-HT2A antagonist known based on an aporphine. Our results also suggest that the C1 position may be a key site for increasing 5-HT2A antagonist activity in this compound series. In addition, the structural rigidity of the aporphine core appears to be required for nantenine to function as a 5-HT2A antagonist. Published by Elsevier Ltd.